


Ash's new career

by Fibaro



Category: Original Work
Genre: Bets & Wagers, Blackmail, Dress Up, Feminization, Makeup, Multi, Sibling Rivalry, Siblings
Language: English
Status: In-Progress
Published: 2020-05-10
Updated: 2020-10-10
Packaged: 2021-03-03 00:07:07
Rating: Not Rated
Warnings: No Archive Warnings Apply
Chapters: 3
Words: 16,733
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/24105673
Author URL: https://archiveofourown.org/users/Fibaro/pseuds/Fibaro
Summary: Ash get's caught stealing a beauty product from his sister's room she was supposed to do a review on. To escape his sisters wrath he rushes to his mother who just so happens to be in dire need of a model.
Relationships: Original Character(s)/Original Character(s)
Kudos: 11





	1. Part 1

**Author's Note:**

> This story was commissioned by a dear Patron of mine, Julia Michelle.

Intro

Ash was a regular though somewhat effeminate looking 19-year-old guy with a not so regular wish as far as guys were concerned. He had always dreamt of being a model, a surf model to be precise. There was just something so powerful about those images from surfer models that had struck him from a young age. The way in which they stepped out of the water their long wild hair neatly folded back by the water, with their board under their arm. It had something magical for him. 

What he would never admit to anyone however was that he truly desired to be one of those babes on the beach. He had always admired the tons of supermodels his mother worked with, their beauty, their elegance and just the sheer confidence that radiated from them. Of course he wouldn’t want to be caught dead dressed in a bikini like one of those girls so it was a desire he strictly kept to himself and even he barely dared think of it. It wasn’t even that he truly desired to be a woman, he was happy as a guy, but the feminine grace and outfits just looked so much better.

Having adopted a lot of his mother’s good genes, who once was a model herself and now ran a modelling agency it looked like he could make it. He had spent lots of time in the gym to get some visible muscle showing. Sadly, it was a hard thing for him to achieve, but through hard continued work he managed. His dirty blonde hair was about shoulder length and went well with his bright blue eyes and great tan. Standing at about 5’9” he was pretty much average in length.

With the aim to match those pictures he Idolised Ash often raided his sister Keira’s skin care products. If he wanted to shine in the role of a hunky surfer, he needed a smooth and spotless torso and complexion. As he had found out rather early nair and moisturisers seemed to do that job perfectly that’s why he used it all over his torso and even his chin. Sadly these products that yielded the best results were aimed at women.

His sister would always get mad at him when she found one of her expensive products missing or drastically depleted. Not that he really cared. Him and his sister had never gotten along. She was three years older than him and had always been able to get the better of him when it got physical. Unlike Ash she took a bit more after their father who was out of the picture. 

Her hair was raven black yet she had the same bright blue eyes as him and their mother. She was built more athletically, only an inch taller than him, but her shoulders were wider and where he had to stick to his training schedule to maintain his muscle tone, building muscle seemed to come natural for her, she could bulk up without much effort.

Keira was a huge feminist and tried her best to break stereotypical gender norms. Unlike her brother she actually had modelling contracts a plenty. They weren’t the contracts their mother had hoped for though. Their mother had loved it when she first had a girl, someone to follow in her footsteps, but from a very early ages already Keira had started rejecting the dresses and pretty outfits her mother had tried to force on her.

The contracts Keira got were nearly always aimed at her looking though. Something that came natural with her athletic figure and short pixie cut. When shooting she aimed to show girls around the world that girls could be just as tough and even tougher than guys. Something which she liked to carry through in her day to day life.

It was her brothers favourite spot of attack. Ash simply loved pointing out that Keira was just a girl while heavily insinuating girls were weak. Afterwards he would have to rush away since Keira could very well beat him up and wasn’t scared to do so either. She had proven so time and time again. Yet seeing his sister pissed was worth it time and time again.

She on the other hand always loved teasing her brother for being a wimp. Although she knew fully well that he was a hundred percent hetero she loved asking him if he was gay. It was just too easy as well the posters of the models he aspired to be hanging in his room as well as his always completely smooth torso and face were pressure points she loved to exploit. He would always get furious, telling her she didn’t understand. Getting furious and yelling at her was pretty much the best he could do since he knew full well that he couldn’t physically take her on. The times he had tried she had simply overpowered him and made even more fun of him.

Their mother Beatrice had long ago given up on trying to keep the peace in the house. Being a businesswoman suited her a lot more than being a mother did. She spent more time looking for the next big contract than she did worrying about her children, after all they were old enough to care for themselves now. On the rare occasion that she did bother with her children’s quarrels, she nearly always sided with Keira, she might not be the daughter she had always wanted, but she did bring in great contracts and her boyfriend Daniel and his family were one of the main investors in her company.

For a woman in her mid-forties Beatrice didn’t look like she had aged a day. At least not when she was fully dressed. Her body was toned and curvy, her hair honey blonde and she had bright blue eyes and a fairly tan skin. Over the course of the years she had had some minor plastic surgeries, together with her strict workout regime, a healthy diet, and a little help from outfits and makeup to accentuate her best features she could easily pass for someone who had just hit thirty.

Chapter 1

Today was a day like any other Ash had just finished his weekly hair removal and moisturiser ritual making his torso shine like never before. He had stolen a new moisturising cream from his sister and he had to admit it was the best one he had ever used before. He certainly hoped she would be buying it more often as he stood in front of his mirror admiring the results in nothing but his boxer shorts.

“Argh you little shit, you’ve been snooping in my room again haven’t you? Now where the hell is my Essence of the Himalaya wonder cream? I swear you’ve better not touched the damn thing or you’re going to be so sorry. I was paid good money to do an unboxing and review on Instagram. Now where is it?” Keira asked clearly pissed, still dressed in her light blue leggings and tight black sports bra, sweaty from her morning jog.

A nervous sweat instantly broke out across Ash’s face. His sister was more pissed than usual, it would only grow worse as well once she found out that he had opened it and used most of the small pot already. With her in his room already he had no where to escape to either.

“Well where the fuck is it you little faggot? I’m not going to ask again.” She said threatingly raising her arm when she suddenly spotted the pot of cream on his desk, still open and next to the packaging that was ripped to shreds. Instantly she rushed over to it, her anger rising as she saw it was nearly empty.

“What the hell did you do you little shit? Do you have any fucking clue how much money you just lost me and mom? Oh your fucking ass is going to be so fucking sorry for this.” Keira screamed as she charged at him.

“I… I’ll give you money to buy a new pot. Besides why do compagnies even pay you to advertise, it’s not like any amount of moisturiser could ever manage to make you any prettier. You might be just a woman, but hell I bet you know everyone knows I am a more beautiful woman than you are.” Ash screamed, holding his arms in front of him to try and defend himself.

Ash wanted to kick himself as soon as he said it. Seeing Keira’s triumphant smirk told him it was a big mistake. In his zeal to get in a painful zinger and win this argument, he revealed his biggest secret to her and now she knew. How could he had been so stupid.

Much to his horror the hits stayed out and Keira stopped her charge, a triumphant smirk suddenly appearing on her face. “Oh yeah? Well bet accepted, now put your money where your mouth is and fucking prove your claim. Tell you what if you manage to prove your claim, I let you off with just repaying the money I missed out on. If you can’t then I guess I’ll just have to beat you and film you for my Instagram story. I bet the whole world would the story about my faggot brother beaten by a girl as his moisturised torso and face are in full view to promote the product. I can already imagine it. Something along the lines of buy this product and your skin will look so good that no guy will be able to keep his hands off you. Tested and approved by my brother who’s just getting ready for his date with a big hunky man.” 

“Nooo! You can’t be serious that was just a figure of speech. Not a real bet! Besides if you just buy a new one the problem is gone.” Ash protested his face going pale at the thought of being exposed like that along with such lies for the whole world to see.

“It isn’t yet on the market you dimwit, I can’t buy a new one. This is meant to be a pre-release advertisement. I do bet they would give me a bonus however if this video I would make went viral which I’m sure it will. Figure of speech or not, a bet is a bet or do you want to fight over it?” Keira asked with a smirk, knowing full well that there was no way in which her brother could beat her.

Seeing an opportunity to make it to the door. Ash dashed out still clad in only his boxer short shouting, “I’m telling mom!” While his sister instantly ran after him, not able to catch up with him before he made it to his mother’s office, barging in without knocking.

“Mom, Keira has become crazy. She…” Ash started off his defence as pissed Keira quickly appeared behind him, but before he could really say all that much his mother silenced him with a quick finger to her lips and a near deadly stare.

“Yes, I know it’s unfortunate, but she really is in no state to appear for a shoot any time soon. Yes I understand, we’re approaching the deadline and I’m trying my best to find a suitable replacement, but models just don’t grow on trees. A fine if I have to break our contract, but…” His mother spoke over the phone when the line was abruptly cut off. “Jack ass!” She shouted in the now dead phone before putting it down.

“Ash you know I don’t want to be disturbed when I’m in my office. You just interrupted a very important call so I better hope you have an extremely good explanation for this.” His mother said annoyed, rubbing her temples. Her mood was already at an all time low. One of her most asked for models had had an accident with her bike this morning. She had fallen flat on her face and skinned one of her cheeks pretty badly. It wasn’t a serious injury, one that would heal eventually, but it would take time for that wound to completely disappear and with such a wound in the face pitching her as a model was out of the question for now.

The firm who had specifically asked for her to be on the packaging of their newest hair products was one they often worked with, and if she wouldn’t be able to find a replacement for the shoot within the week she would be screwed. This was a very competitive business and this firm had many contracts with her agency. They had just threatened to pull them all while also fining her. This disaster could mean she lost a quarter of the yearly income.

Her son stood there lost for words, he knew he had just screwed up big time. He could tell his mom was already in a foul mood, and he doubted she would find his reason for barging in here acceptable. Shit he was in so much trouble.

Eventually he spoke up, hoping for the best as he started explaining the situation. “Keira here threatened to beat me up and expose me for the whole internet. She has really become crazy. You have to stop her.” Ash whimpered.

Keira immediately objected. “He fucking snuck into my room and stole that pot of Essence of the Himalaya wonder cream that I was supposed to unbox and promote on my Instagram. It’s completely destroyed and empty and isn’t yet on the market either so there is no way I can do this contract now. He then bet and these are his exact words that everyone knows he makes a more beautiful woman than I do. I took on his bet and told him to put his money where his mouth is, or that I could just film him for my Instagram story to show of what their product can do on his chest. I bet that would go viral and would earn some extra on that contract.” 

She knew contracts where sacred for her mother and since not only she but also her mother could lose money over this she already knew her mother would side with her. She could see on Ash’s scared face that he knew it as well.

At first Beatrice’s blood started boiling. That contract her daughter had been talking about was one with the same firm that she just got off the phone with. They were already threatening to cut all their contracts for not being able to deliver with the model they requested. If she had to tell them there was yet another problem her income would be screwed and the reputation of her agency could get severely damaged. She really couldn’t afford this right now.

Then all of a sudden the full extend of the story hit her and slowly but surely an idea started to form. She had always known her son was somewhat effeminate. Hell he was pretty rather than handsome, one of the main reasons while his so claimed dream of being a surfer model would never work no matter how hard he tried to get in shape. He just didn’t have that handsome manly face to go with the smooth torso, and no where near the muscle mass required either, no matter how much he trained.

With some makeup, as well as good poses and the right angles, she believed that her son could probably convincingly pass as a pretty girl. In fact she was quite sure of it. He also had full well taken care of blonde hair like the model who had fallen on her face. Maybe just maybe she could manage to pitch him for that contract, it would safe her agency from a big loss and maybe she would even be able to make a good profit out of it.

After all in this present time there was a big demand for models of all sort, transgendered, full figured, hell even butch ones like her daughter. All sorts of companies tried to diversify the models they used in their advertisements as much as they possibly could. Having a pretty “trans model” under her agency could give her a big boost in contracts. This could prove to be a perfect opportunity if she played her cards right.

In a matter of seconds Beatrice’s ready to explode look changed to a big smirk. Although it should be a relief that smirk was scarier to Ash than the anger had been. What the hell had made his mother suddenly change like this?

“Well Ash, I think your sister is right. You should put your money where your mouth is if you’re making bets like that. You should pay up by either winning or taking the consequences of losing. We are no family of losers though so I insist you’ll first try to win.” Beatrice said looking into her shocked son’s face while her daughter was smirking broadly in the background.

“You are right on one thing though Keira is crazy to just expect you to prove your claim right on the spot. We women have had years to figure everything being a woman entails out. It would be crazy to think you could just show your claim right away. The least we should do is give you all the tools and help to prove your claim.” Beatrice continued

“We’ll help you with your makeup, your outfit, then do a little shoot to compile a modelling portfolio and put it next to that of your sister. We can then ask some of our models and photographers who work for us their opinion on who they think makes the more beautiful woman. Of course won’t give away your identity so their opinion won’t be biased. I think that’s the fairest method of approach. Of course since you made the bet with your sister we should ask her if she agrees to these terms, or if she really believes you should just prove it now or appear on her Instagram.” Beatrice finished.

Ash was shocked, sure being a gorgeous model had always been a dream of his, but he was too ashamed to tell anyone. He sure as hell didn’t want his mother and especially his sister to see him like that. He simply wouldn’t hear the end of it. Let alone letting others see him like that or worse take pictures. His mother hadn’t even asked if he agreed to those terms. In the bigger picture this sure would be preferable than being beaten up by his sister and called a faggot for the whole internet to see. It was something that would haunt him for the rest of his days. Everyone would only know him as that faggot who got beat by his sister. Compared to that a semi anonymous portfolio was definitely the lesser of two evils.

Keira’s smirk had only grown during her mother’s explanation. Giving her brother a make over would be so much more fun and satisfying than just humiliating him on Instagram. Hell if she could get her hands on that portfolio as well then she had him right where she wanted him. There was no way he would ever be a nuisance to her anymore if she could threaten to spread that thing. 

In fact she could use that portfolio to push her own agenda as well. One of the photographers had been bugging her for ages to do a ‘special shoot’ with him. Everyone knew he was a big perv though and there was no way she would ever agree to his offer. An offer he made to pretty much every model in the agency except for the male ones. He was such a perv that most models were reluctant when they knew he would be shooting, sadly he was a genius with his camera and so her mother wouldn’t even think of firing him. Maybe if she could make Ash appealing enough she might be able to switch his focus to him, have Ash agree to his ‘special shoot’ so maybe he would leave her and the other models alone.

If she managed to make her brother really pretty she might even manage to get her asshole of a boyfriend Bruce to develop an interest in him. He was an asshole from a rich family who her mother had hooked her up with. His family was one of the big investors in her agency so she couldn’t just break up with him or her mother would be angry out of her mind. 

Sadly she and Bruce had very different ideas of what a woman should be like. While she was all for the butch look, female empowerment and independence, he thought a woman should just look pretty and be obedient. His mindset was still stuck in the 50’s and the only reason he got away with it was because his family was rich. Oh how she wished she could beat him up. Her mother would probably kill her if she did which was the only thing stopping her.

Up until now she had managed to keep true to her ideals and looks for the most part. It wasn’t something she was willing to change either, but Bruce was getting more and more impatient and demanding. She was pretty certain she soon would have a choice to either give in or breakup, and a breakup was something her mother would never allow. Unless of course she could make Bruce fall for a prettied-up Ash. She was certain that her mother didn’t care about who exactly was with Bruce, just that his family stayed tied to hers for their investments.

Keira was extra motivated to make Bruce fall for her brother. Not only would she be rid of the asshole, she would also finally be able to bring her secret relationship with Ellen, another one of her mom’s models out in the open. With that in mind she replied. “Oh you’re absolutely right mom, It was crazy of me to be expecting him to just prove it. We have to give him all the chances we possibly can to make him the prettiest possible girl before we pass judgement.” Keira eagerly said playing right into her mother’s cards.

“Of course we do need professional help to give Ash the best possible chance. So Keira while I fix a photographer, a makeup artist, a stylist and a hair dresser why don’t you teach your brother the basics? The shoot probably won’t be for today anymore, but that way Ash can get into the role a little already. “Beatrice said with a smile before waving her kids away as she started dialling on the phone, making clear no discussion would be had about it. Keira was all smiles and a stunned Ash was too afraid to interrupt his mother again.

Looking forward to having some fun at her brothers expense as revenge Keira grabbed Ash’s hand and started leading him down the hall again. “Oh mom is so pissed, she sounded like she was about to lose a big contract and then you barge in screaming and basically admitting you screwed another one of her contracts. I don’t know what mom will do if you screw up again, but I’m sure it won’t be pretty.” Keira said with a huge smile, rubbing the situation in further to ensure Ash would be very compliant when she got to work.

On the short walk to their rooms Keira was thinking about what kind of style she wanted for her brother. One thing was for sure, it should be a rather extreme style as she really wanted to get the most out of embarrassing her brother now that she had the chance and her mothers blessing. There was no way Ash would normally agree to let her do anything to him, but being able to threaten with telling their mother would prove a powerful tool right now.

Keira choose to march her brother into her own room simply because she had a vanity table an he didn’t. If she wanted to teach him all the tips and tricks of using makeup then a good mirror would simply be a necessity. “Alright little brother of mine, let’s start with your very first makeup lesson shall we?” Keira asked as she forced her brother to sit down in front of the vanity table, still clad in nothing but his boxers.

“First and foremost, we need to get you makeup ready. The first step would be to use a good hydrating facial cream, but since you already used one of mine, even on your fucking torso I guess we can skip that step which leaves us only with those bushy brows of yours.” Keira said with a broad smile as she picked up a pair of tweezers.

“Keira, please don’t, just be reasonable for a moment they won’t just grow back after you gave this stupid bet of sorts which you know was just a joke it’s best try. God knows how long it would take until that damage is gone.” Ash spoke nervously and genuinely scared of his sister.

“Joke or not, you shouldn’t have said that if you didn’t mean it, besides as I recall it, it didn’t even sound like a joke at all. I know those brows will take time to regrow, but just think about it, we can’t give this our best shot if we leave your brows as they are now can we? If you really think I’m being unreasonable we could go back to mom and interrupt her phone call again. I bet she will be thrilled to confirm that we really should take care of those brows of yours.” Keira offered with a smile knowing full well she had the upper hand.

Ash realised full well if they went to interrupt their mother once more he would be into a world of trouble so he nervously stammered.” N…no, that won’t be necessary.” He was more scared of his mother than he was of how visible this change Keira might make would be. It wasn’t even that he was against getting his eyebrows plucked. He was just scared that everyone who would see them would know of his deepest most secret desire.

“Good, then sit still as this is only going to hurt a bit.” Keira smiles as she moved Ash’s head back none too gentle, a bit surprised as she gave his eyebrows a closer look to find in a pretty neat state already. There were no stray hairs to be seen, yet they were rather full and thick. Too thick for the look she wanted her brother to have so she started plucking away. Her brother was a bit of a freak when it came to immaculately maintaining his appearance so the neat brows weren’t that out of the ordinary.

By the time Keira was ready allowing him to look down Ash was horrified. There was nearly nothing left of his eyebrows, nothing but two extremely thin high arches. Although he had secretly like the thought of having a bit more shapely eyebrows he really didn’t like what his sister had done with them. Eyebrows this thin had been out of fashion for ages, they were simply horrible.

“I’m so glad you like them. Ash, they are so you, now watch carefully as I apply your foundation, cause once I’m done with your makeup you are going to redo it yourself.” Keira said with a big smirk enjoying the shocked look on her brothers face. Revenge was so sweet.

Ash’s horror only grew as he witnessed how his sister completely ruined his face with the tasteless tarty sissy makeup she applied while telling him how he had to replicate the look. The foundation she used was way to pale for his skin making it look nearly porcelain white. It was followed by colouring his newly plucked arches in way too dark, the pink lip liner she used deviated way too far from his actual lips looking fake as hell instead of just enhancing the lips. The bright pink colour lipstick and overdose of gloss only made it worse. For his eyes she chose exaggeratedly large wings paired with mascara and a solid colour of pink eye shadow over his entire eyelid before finishing the look with two deep pink circles on his cheeks. Ash ended up looking like a weird combination between a hooker and a porcelain doll and he simply hated it, something Keira delighted in.

“Tada, you’re all ready. Just look at you such a pretty doll, Maybe you are right and you do make a prettier girl than me. What do you think should we take a selfie and ask my followers?” Keira taunted giving Ash the scare of his life there was no way he ever wanted to be seen by anyone like this.

“Maybe we better wait though cause I don’t want to get banned for indecency because my pretty little brother is showing some nipple. I bet you look so convincingly that they would think you are a girl and we all know girl’s nipples aren’t allowed. Just wait here while I find you a fitting outfit to go with your new look. While I’m busy with that I want you to try and replicate this look on your own, after all a girl needs to know how to do her makeup. There are some wipes over there, just follow what I thought you and you should be fine.” Keira taunted as she was already looking forward to the final result. Surely it would be badly applied on top of being tarty making it look even worse. She couldn’t wait to see that.

As fast as he could Ash grabbed the wipes and started carefully removing every trace of the makeup his sister had slathered on. He just couldn’t stand the tarty face starting back at him and he couldn’t be rid of it fast enough. Expertly he wiped his face clean in less than a minute. A skill he had picked up when he sneakily tried to put on makeup before, but had to get rid of it quickly not to get caught.

With that horrible makeup job finally gone Ash started reapplying the make up as he had been ordered to by his sister. He knew he couldn’t deviate from her look too much so he had to use the same products in order not to raise too much suspicion, but there was no way he was going to allow his face to look that tarty again.

The foundation still was way too pale for his skin, but he kind of fixed it by applying a way lighter coat, making his own skin shine through way more giving him a darker toned end result. The brows were pretty much a lost cause having been plucked way too thin, yet with the help of the eyebrow pencil his sister had used to turn them really dark he managed to outline new fuller brows, going easier on the colour to make them appear more naturally again. 

His sister who turned around with a smirk from her closet, looking for the perfect outfit, but not wanting to miss the chance to see her brother struggle and fumble with his makeup ended up being rather surprised. Ash in fact looked rather calm and collected applying the makeup not perfectly, but certainly with a certain skill. From what she could see now he was also doing a better job or at least a less tarty job of his makeup than she had given him.

This made her think back to her earlier confusion about his neat brows, and the confident way in which he had said he would make a prettier girl than she did. The previous two things she had been able to explain for herself, but for this makeup there really was no explanation. Her earlier suspicion’s returning in full force Keira decided to sneak off to her brother’s room instead to look for some confirmation for what she suspected.

Ash was so focused on his makeup job that he didn’t even notice Keira leaving the room. Instead he redid his lips, simply outlining his lips with the pink lip pencil, giving the illusion of being slightly more voluminous before applying the same bright pink lipstick but only using a hint of gloss giving his lips a healthy shine. For his eyeliner he resorted to simple top and bottom lines with tiny wing as an accent before applying the mascara. For his eyeshadow Ash resorted for a deep intense colour close to the eye which grew gradually lighter the further from the eye it went making it look far classier. Finally for the blush Ash carefully applied a little dusting highlighting his cheekbones more than anything.

Leaning Back Ash was rather pleased with himself. While the colour scheme was not something he would have personally chosen he had managed to turn the look his sister had insisted on into something somewhat more classy and definitely more natural looking. 

What Ash didn’t know however that his sister had gone up to his room and had actually found the outfit he had carefully hidden away. It consisted of a simple dress, a very sexy lingerie set that Keira had once worn for a photoshoot she had wanted to refuse, but her boyfriend had insisted she’d do because it looked ‘hot’ and a pair of strappy sandals. 

Her suspicion that Ash might actually secretly like this was confirmed, but seeing how strongly her brother kept denying it she could definitely tell that he didn’t want it found out at all. This was even better than she had initially thought as it meant she could now use that secret as leverage over her brother to push her own double agenda she had with the photographer and her boyfriend. 

With proof of his secret in hand Keira walked back to her room with a big smile. Ash certainly had a lot of explaining to do, and he had a good reason to stay in her good graces as his secret staying a secret now entirely depended on her silence.


	2. Part 2

Chapter 2

Standing back in the doorway of her own room Keira was surprised to see the wonderful job Ash had done with his makeup. It looked nearly as good as her own best effort despite the colours she had given him. She smiled watching how Ash applied the last touches to his makeup look before coughing loudly just when he was putting the brush down. 

Ash who had been so absorbed in applying the makeup as good as he could shook out of his concentration and looked over to his sister in the doorway. His facial expression instantly turned to one of shock as he recognised the outfit Keira was holding perfectly. It was the very same outfit he kept hidden away in his room.

With Ash looking at her it was her turn to be surprised. If you only looked at the head he actually looked shockingly girly, he had never looked the most manly with his clean shaven babyface. The makeup paired with his longish hair really had something cute though. He looked almost like their mother did, although in a way younger, way less curvy version. The boxers and his slightly visible abs kind of ruined the cute girly look, but that would instantly be solved by the outfit Keira had with her.

“My my Ash, don’t you look pretty? If I didn’t know any better I would believe I had a sister. Maybe there is something to you making a prettier girl than me after all. I mean especially with the way you so skilfully applied your makeup and with this cute outfit I found in your closet. Guess I was right and you have always been a big sissy after all. I wonder what mom would think, or your friends if I showed them this.” Keira smiled playing on Ash’s insecurities. From his reaction she could see that the fear of exposure was indeed huge. It told her she had him right where she wanted him.

“Please Keira, don’t I beg you. My life would be over, please don’t tell anyone about this I beg you.” Ash exclaimed in panic. He always felt happier when dressed as a girl, it was one of the reasons he had taken the risk of keeping an outfit stashed away in his closet. Yet the thought of how people he knew would react if they found out about this side of him terrified him. 

“Well I don’t know Ash, this is actually a pretty huge deal. Don’t you think people have a right to know? I bet they would be so very shocked, god I wouldn’t dare face anyone if I had such a secret.” Keira said slowly, deliberately fuelling his fear so Ash would be easier to control.

“Although I guess I can help out my little brother, or should I say sister? I’ll keep your secret, but in exchange I’ll expect you to be a very good b… girl for me. One misstep and I won’t hesitate to expose your little secret to everyone. For starters you can put on your pretty outfit for me, everything including those racy lace panties.” Keira said with a smirk as she handed the clothes to Ash.

Still shaking that his sister had found out his secret Ash took the clothes and nervously put them on. He had put on this very outfit countless of times but doing it now to be seen it felt so very wrong and bad in a way. It was his secret guilty pleasure, no one was supposed to see him like this it made the oh so familiar outfit feel almost alien to him.

At least his sister did give him some privacy to get changed, turning her back towards him. Just in case she would turn back around Ash quickly switched his boxer shorts for the white lace thong that came with the outfit. It always made him feel sexy, but now he felt more exposed than anything else. The panties were quickly followed by the matching white lace garter belt, the sheer white stockings with white lace tops which Ash was able to attach to the garters without much effort at all. Even the push up bra that came with the outfit went on without effort.

Once Keira felt somewhat certain that her brother would at least be partially dressed already she turned around, unable to wait any longer to see what he would look like. The slight hint of abs Ash had were still a bit of a distraction from the overall girliness, but the sexy lingerie did form a great distraction from them making Ash look more like a cute girl than a guy.

Keira’s grin only grew when Ash put on the light pink summer dress with a skater skirt reaching till right above his knees. His abs covered and the sturdiness of the cups of the push up bra, tenting the dress a little at his chest really completed the look, covering up the last giveaway’s rather decently. The white strappy high heeled sandals just finished the look.

“My my, just look at you Ash, or wait. Ash doesn’t sound right for a girl this cute. Ashley, yeah let’s settle on that. Just look at how cute you are Ashley now why don’t you give me a twirl so I can have a better look?” Keira asked with a smile watching as Ash nervously preformed her command.

“Awe, just like a prima ballerina. Now let’s go and see mom. I bet she’ll love to see her new daughter.” Keira said with a big grin as she walked over to Ash and put a hand on his shoulder just in case he would try to run.

“Nooo! Keira, mom can’t see me like this. You promised that you would keep my secret if I did as you said. Mom can’t see my like this.” Ash instantly blurted out in panic as she looked back at his smirking sister.

“Of course mom can see you like this Ashley. That’s the whole point, especially since you made a point out of involving her in that bet you made. Now the choice is yours, either I’ll go show you to mom like this showing her what a good job I did on your makeup and what a cute outfit I selected for you.” Keira said sternly leaving a long pause.

“Or I could force you along to mom’s office and show off what a well-practiced makeup look you pulled off. Then I can inform her that I found this cute outfit with this sexy lingerie in your closet, telling her you must really be one big sissy and see how she reacts then.” Keira said threating using Ash’s fear against him.

Giving her words a moment to sink in she then asked. “So what is it going to be? Are you going to follow along quietly and let me take the word or are you going to interrupt and protest, so I’ll have to expose your little secret?” Keira asked already knowing what the answer would be.

Ash was stunned. His sister was right though her mother had approved of Keira dressing him up so if he showed up like this she wouldn’t really think much else about it, not unless Keira gave away his secret and he didn’t want to risk that. “I’ll come along quietly.” He eventually softly replied.

“There’s a good girl, I knew you were going to come to your senses. Now let’s go show mom her cute new little daughter. I’m sure she will simply be delighted.” Keira grinned as she pushed Ash in front of her, guiding him to their mother’s office where she knocked on the door. A quick come on in followed soon after.

With a proud smile Keira opened the door pushing her prettied-up brother in front of her in front of their mother. Beatrice instantly looked surprised she had seen the potential in Ash to make a pretty girl, but she hadn’t expected her son to make such a pretty girl with just some makeup and an outfit. It gave her very high hopes that he would make the ideal replacement for her model who was currently out after her accident. If she could launch her son as such a gorgeous trans model she could get tons of big contracts for her agency. This could turn out to be really profitable.

Giving Ash a thorough once over she had to admit that Ash did make a prettier girl than his sister did, way more of a girly girl, like the daughter she never had. Of course she wouldn’t say that, not yet at least or Ash could claim he had won the bet already and her chance of turning him into one of her models would be ruined.

“So mom, what do you think? I tried doing his makeup and to find him a nice outfit. Oh and before you say anything. I don’t think Ash is a really suitable name for him or should I say her? Ashley is a way better name don’t you agree?” Keira asked proudly, keeping her word and taking credit for his makeup and outfit so their mother wouldn’t expect a thing.

Ash was only slightly relieved that Keira held her word, but at the same time he was worried. He didn’t want to be called Ashley yet he also knew that what he wanted here wouldn’t matter. Making a fuss about it might end up making Keira reveal his secret after all and with how helpful his mother had been so far he could only guess she was all for the name Ashley.

“Well Keira I have to say you did a great job already, Ashley looks quite good. If I were you I would be worried cause with some professional help like for the shoot tomorrow Ashley could really end up looking prettier than you.” Beatrice said, trying to limit her praise of Ashley’s looks so it wouldn’t ruin her plans.

To Ash it came as a big surprise, unknowingly his mother had complimented his makeup skills and he didn’t know how to feel about it. Somewhere deep down he was proud of it, but he shouldn’t be right? God this was so confusing. 

While Ash was confused about their mothers small compliment Keira wasn’t all that happy. She didn’t actually want her brother to make a prettier girl than she did, no she wanted to humiliate him and pay him back because it was unfair how easy his life had been up until now. It was unfair how he could do as he pleased while she was pressured into being a model and a girlfriend to that jerk of a Bruce.

“Just a quick dress up doesn’t really prove much though. There is so much more to being a woman than just putting on a dress and makeup. I think Ashley should at least stay a girl until after the shoot so I can teach her some more about what it is like being a woman.” Keira said tightening the control she had on her brother.

“I think that’s a great idea. Ashely for your own good you should listen to your sister. You do want to win that bet don’t you? In fact after your claim I think it’s only fair that you do your very best to prove it or I’ll be angry. Now the two of you can go, I still have work to do.” Beatrice said agreeing to Keira taking full control like Ash had feared.

Quietly they left the office, closing the door behind them as Keira whispered in Ashely’s ear. “Did you hear that sis-sy? You get to be my sister all day long and I will personally see to it that you learn all there is to learn about being a woman. Now you better play along nicely or I might just let your secret slip to mom.” Keira grinned, even though Ashley couldn’t help it she was going to regret being complimented by their mother.

Back in her office Beatrice was smiling. While walking out she hadn’t been able not to notice how good Ashley actually walked in those heels. It was quite surprising to be honest. Anyways, it was time for her to call the company behind that big contract to let them know she most likely had a replacement model. If she played her cards right, she might even pitch a better price since she could give them a transgendered model. After all diversifying your brand was key these days and rightfully so.

While Beatrice was making numerous phone calls to hairstylists, makeup artists photographers and editors to get everything ready for Ash’s shoot tomorrow. Keira was having some fun at her brothers expense. She had to admit that Ash looked very pretty, possibly prettier than her even and while it would be perfect of coupling him with Bruce and that asshole photographer, she couldn’t stand it. She had hoped he would look more like a clown with his fully made up face, that he would look ridiculous but since that wasn’t the case she would have to find another way to make him look ridiculous.

That new way to make him look ridiculous was an exaggerated mannerism training. While Ash knew how to walk in heels decently well from learning to do so in his room, she still insisted that he adopted a swishier mincing step. She wanted to make him look like a caricature instead of a real girl. At first Ash protested heavily, but under threat of his secret being revealed he eventually caved in, following along with his sisters mincing and curtsying training. 

He knew that this was not how a girl walked, just like the makeup Keira had applied to his face was outrageous, but under threat he had no choice but to follow along. He wouldn’t stand for this though. As soon as Keira wouldn’t look he would go back to walking graciously like he had taught himself, just like he had redone his Makeup way better than when Keira had applied it.

Sadly for him Keira watched him very closely most of the day. She was enjoying this way to much not to do so. When she eventually grew tired of playing with her dolled up brother she decided it was time for him to go to bed, not caring that it was way earlier than he usually went to sleep. “Alright Ashley, time for you to go to bed, tomorrow is a big day after all and you’ll need your beauty sleep. Besides such a prissy girl like you needs time to get ready for bed.” Keira teased.

“First things first, strip out of your dress and heels. Then you can clean off that makeup, give your face a nice scrub, then use this moisturising cream and finally apply this paste for your night-time beauty mask.” Keira instructed handing Ash an arm load of products to get everything done as required. This part wasn’t actually so bad for him. He had used that scrub before and that moisturising cream as well, but never the mask. He had always kind of wanted to try it, but he had been too scared of being found out. Afterall the green mask needed to stay on for a while to have an effect so if anyone would enter his room for any reason he would have been screwed.

Now was the perfect opportunity though. Although it was still somewhat embarrassing to be seen with such a facial mask his sister had just given him the perfect excuse to fully indulge in a night-time skin care treatment. He tried not to show it, but he eagerly put the products to good use. 

Once he was done Keira was right back with her next demand. “Alright, now for the final piece, your nightie. It isn’t really part of the set, but Bruce bought it for me once, demanding I’d wear it with this set. I never did and now it’s yours.” Keira smirked handing Ash a sheer white nylon baby doll nighty with a feathered top and bottom hem. Although it went from his upper chest to his upper thigh the nightie didn’t hide a single thing. His lingerie was still perfectly visible underneath.

To ash it was embarrassing and way too sexy to wear here with his sister, but he gave in either way. At least alone in his room he wouldn’t mind wearing this and his room was right where Keira took him. “Now my sissy brother, it’s bedtime for you. Afterall it’s already 8 o’clock. Now if I hear or see you get out of bed then I’ll be marching you straight to mom like this and you can tell her goodnight. I bet she’d love to see this.” Keira threatened making sure he would be staying in bed even though it was way to early.

Her threat worked wonders as Ash remained in bed during the entire night even if sleeping in had been difficult. Not only had it been way too early, he was also secretly excited yet worried about his shoot. It was a secret dream come true to do such a shoot, but he desperately wanted his secret to remain secret as well. 

Chapter 3

The following morning Keira enthusiastically entered his room without knocking. “Oh Ashley, it’s time for your big day. Now we have no time to lose. I want you looking and smelling your Sunday’s best when we arrive at the shoot. I already ran your bath for you.” Keira said as she pulled the sleep groggy Ash out of bed, leading him to the bedroom clad in nothing but his sexy lingerie. 

Helping him remove the face Mask Keira demanded him to strip completely naked after handing him a simply white bikini’s bottom. She really didn’t want to even see her brother’s genitals so he would just have to bath in the bikini. “We’re leaving for the shoot in two hours mom informed me last night. We still have to properly wash you and your hair, and of course pick you something to wear. Luckily we don’t have to do makeup or anything. They’ll be doing that on site.” Keira said as she barely left Ash any time to process things. Once he was in the bikini bottoms she pushed him into the bath which smelled strongly like strawberries.

“I hope you like the scent, I specially selected it for you. The fruitiest products I could find so you can smell like just as big of a fruit as you are.” Keira laughed as she let Ash soak for a while, allowing the scent to permeate his skin. She then took the shower head and started washing and conditioning his hair using strawberry scented products just like in the bath. She loved treating her brother like a helpless doll.

Pulling Ash out of the bath she blow-dried his hair adding a lot of volume and making the already long hair for a guy look extra girly. It didn’t really matter that much since the hairstylist would be taking care of it, but Keira really wanted her brother to look as girly as possible upon arriving at the shooting location already.

“Normally models just arrive in something comfortable for the shoot, but you aren’t just normal right. You should look your girly best Ashley, follow along.” She said before walking off to her own room with Ash in tow. Laid out on her bed was a set of sexy lingerie paired with his white high heeled sandals and a rather revealing outfit.

The lingerie consisted of sexy white lace thong cut panties, a matching bra and a garter belt paired with nude coloured stockings. Accompanying it were his white high heeled sandals, a soft pink skater skirt and a white crop top. Obviously his sister wanted him to wear different clothes than yesterday. With how tomboyish her usual wardrobe was it was also obvious that she had gone out of her way to find one of the girlier sets of clothes she owned. She never bought any skirts or dresses and doing shoots for those was pretty rare as well. Most of the time she could appease Bruce’s demands by taking lingerie shoots he liked those more anyways and they shut him up for longer. 

“That’s too much Keira. Isn’t it bad enough that you made me smell like a fucking strawberry already? What would the shooting team say if I arrived in a full set of lingerie while you claim that models always arrive in something comfortable. Don’t you have a pair of leggings or such? Something more you know, casually comfy?” Ash complained.

“Oh absolutely not Ashley, you are going to wear these clothes and nothing else. They are going to think you’re a big sissy, and rightfully so. Of course mom will know I dressed you so your secret will remain safe, unless you keep being so difficult. I can always lay out a couple more lingerie sets and go complain to mom that you are going to make us late because you can’t decide which set looks sexier. Of course after letting her in on your secret that is.” Keira said with a smirk, knowing her brother would give in.

“Alright, but only when you make it very clear to everyone that you picked out this outfit.” Ash tried to bargain. If Keira took the blame then maybe he could save his secret, at least for now. He didn’t like having to appear like this in front of his mom and the full shooting team, but only out of fear of being found out. If he had been alone he would have loved putting on this outfit.

“Well of course Ashley as you wish. Now just get dressed, I’ll turn around for a moment, but it is almost time to leave.” Keira said loving her control. She could hear here brother groan which was a delight to her. She wanted her brother to suffer the same things she had had to suffer all these years. Having to dress up way girlier than you’d want or doing stupid shoots you don’t want to do. Her brother had always had the easy life as far as she was concerned. 

Turning back around after she was confident that her brother was at least wearing the panties already Keira couldn’t help but notice how skilled he was at attaching garter straps to stockings, he was even better at it than she was. “My my, you sure are pretty skilled at that, it looks like a well-practiced move, not that it’s all that surprising after what I found in your room.” She mocked making him blush as he connected the last straps to his stocking top. 

Once he was fully dressed Ash’s nervousness only grew. He feared being seen like this by others, the fact that Keira would take the blame was only a small relief. After all, what brother let his sister do this to him? With Keira’s threats and the fact that she was simply stronger than him he didn’t have much of a choice but to go along with her antics.

No one knew it, but the fact that his sister was stronger than him despite all the exercise he had gotten in, accomplishing nothing but some lean muscle were all testimonies to the great extend he had gone to to hide his secret. The lack of muscles and a lot of body hair were blamed on very late puberty and genetics. With how Ash exercised and even the fact that he had found himself a girlfriend. He had covered up the fact that those so-called genetics were his own doing. He had been taking underground hormones for a while now, not wanting to bulk up or get dark hair all over, mainly testosterone blockers as he didn’t want to start developing in a more feminine way either. That would have brought out his secret for sure.

He had noticed a slight swelling and increased sensitivity in his nipples lately. The change was a very subtle one, but it made him worry that those underground hormones he got might not be exactly what they said they were. After all with the unlabelled canisters of pills he couldn’t be sure. He had taken the risk however since they had so far proven to work at preventing his bulk up and delaying the growth of big amounts of body hair.

“Come Ashley it’s time to go!” Keira suddenly exclaimed yanking Ash out of his thoughts of how he had gotten himself in this situation. His constant safeguarding of his secret had directly led to it now being brought in the open. It was almost poetic how he was practically forced to live his dream, a dream he had hidden for so long. It was like the universe was forcing him to take the first step to acceptance.

That didn’t make this whole situation any less scary though. As they approached their mother his nervousness came to a peak. “My my Ashley, couldn’t wait to get dressed up? Don’t worry, there’ll be plenty of dressing up at the shoot for you. At least you didn’t put on makeup yet, good, it’s best to leave that to the specialists. You even smell pretty.” Beatrice said with a curious smile having expected her son to wear something simpler to go there.

Ash didn’t know what to say to that, but fortunately for him his sister kept her word. “Oh mom, with Ashley’s claim of how she could be prettier girl than me I couldn’t just let her put on a legging now could I? No, real pretty girly girls should look pretty all the time” Keira explained, it wasn’t the taking the responsibility Ash had hoped for, but it was something at least.

“You’re right Keira, if Ashley makes such claims then she should bear the consequences. Now it’s time to get going, or shooting location is still a little drive away and we don’t want to be late. Those professionals are costly and paid by the hour.” Beatrice said, her amused tone switching to a more serious one. As far as she was concerned Keira had the right to poke some fun at her brother after his claims. Ash did make a rather pretty girl though, even without the makeup for some reason. The chance that she would have her replacement model was looking ever more likely.

Getting into the car they drove off to their lake side house. It was one of the perks of the modelling agency Beatrice ran. Technically the house was company property, a shooting studio with nice settings to shoot all around. That had never stopped them from spending vacations there though. Those vacations had always been memorable unlike for Keira who had done shoots there rather often it was nothing but a vacation spot to Ash.

Upon their arrival there was one car on scene already, the others would probably be arriving shortly. Getting out of the car Beatrice instantly went out to greet the woman who was standing near it. The woman was of average height with a dark blue nearly black pixie cut wearing a pair of simple grey leggings, a black tank top and black sneakers. Getting out with her brother Keira was a little confused. She had done enough shoots to know all the regulars her mother hired or had under her employment. She didn’t know this woman though.

“Ah Ashley, come over here a minute. I would like you to meet Jessy, Jessy, this is my son Ash or as we’ll call him today Ashley. Jessy here will be your makeup artist and we were lucky to be able to get someone with her talent on board for today.” Beatrice introduced them as Jessy subjected Ash to a studying look. Ash was mortified though. Of course the people working on this project would know he wasn’t really a girl, but to be introduced like this was simply embarrassing.

Jessy’s studying look soon went over in a warm smile. “Ah Ashley so nice to meet you, your mother is really big on the compliments, isn’t she? It wouldn’t take much talent to make you look good for the camera.” She said embracing Ash in a quick hug while was simply stunned. She didn’t think this was strange?

It didn’t take long for Keira to interrupt the greetings. “And who are you exactly? You aren’t our regular makeup artist and I don’t know you.” She said a bit blunt in her confussion. She was already looking to introducing her brother as Ashley to the people she frequently worked with and now this new girl showed up.

“Well I’m no regular makeup artist either. I specialise in transformative makeup although it’s a bit more than that, I like to call myself a bit of a body sculptor. I’ve worked behind the scene for drag shows from time to time but I specialise in more realistic transformations. I have my own little studio where I help men, closet crossdressers or closet trans folks realise their dream of looking as realistically feminine as possible. Makeup is one part of that, but there’s so much more to it. For a lot of these people it’s hard that they can’t be who they want to be at least not freely so when they visit me I like making their dream become true, using all the tricks I know. For a lot of my clients it’s amazing to see their womanly potential and during the shoots after their transformation we make some fond memories for them to cherish.” Jessy explained. 

“This is the very first time I’m working for a real professional shoot though, but well like I said it won’t take much talent to make Ashley look good for the camera so in that regard I’m more than ready.” Jessy said with a warm smile.

While Keira smiled in delight, hearing that her brother would get a very thorough makeover, Ash himself looked shocked. Not because of what Jessy was here for, but more about the professional shoot. This was just for a portfolio, right? 

Seeing Ash’s concern Jessy spoke up again. “Hey don’t you worry, It’ll be fun, I promise. Nothing to be nervous about. We’ll just make you look even better in that cute outfit you’re wearing.” Jessy said trying to appease Ash. This wasn’t to Keira’s liking though, she had hoped Jessy would go more of the drag way. She wanted her brother to look over the top, not like just another girl. It didn’t appease Ash either as it was the professional shoot he was worried about.

The next one to arrive on scene was Dean together with Sarah. They didn’t need introduction as Keira immediately greeted them. “Ah Dean, Sarah, so good you guys are here. I would love to introduce you to my bro… uh my sister Ashley, she’s the model of today’s shoot.” Keira said instantly taking charge as the couple coming out of the small van giggled lightly. Dean was a tall man, with a stylish brown hairdo, short on the sides and longer on top. He would be the photographer.

Sarah his wife was a pretty blonde with straight hair looking like she put a lot of effort in her appearance. She had met Dean through her work with the modelling agency of Beatrice where she was the regular hairstylist. 

Keira had only just greeted them when another van arrived. A tall dark-haired woman of middle eastern descend got out. She was here to provide the wardrobe as ordered by Beatrice. “Ah Jolene, good you are here. So with everyone here I think we can start getting Ashley ready for her portfolio shoot.” Beatrice announced, taking the lead to get everyone to move into the lakeside house. 

Ash just followed along slightly overwhelmed. He had secretly always dreamt of becoming a model, but he hadn’t anticipated this. He was rather surprised that there were so many people here just for his shoot, and honestly it scared him a little, all these people seeing him as a girl. It might have been a dream come true in the strict sense, but right now it felt more like a bad dream, why couldn’t a shoot just happen with him alone in his room?


	3. Part 3

Chapter 4

Sensing Ash’s nervousness Jessy took charge upon entering the house. She had the feeling that something wasn’t quite right with this shoot, but most of all she wanted to appease Ash a little. “Alright, if you all don’t mind I have a lot of work to do and I rather do so quietly, well at first at least. Once I’m ready with the foundations I’ll call in Sarah to start on the hair, I’m pretty sure the rest of you know how to stay busy setting up the equipment and scouting the best locations.” She said firmly.

It wasn’t much of a problem for Jolene or dean. Jolene just needed to unload the clothes in the sizes Beatrice requested, then go over them with her to select the outfits. Dean had a lot of work setting up all his camera equipment anyways. For Sarah it was a slight adaptation as usually she went to work along with the makeup artist, but she could understand that making Ash look like a proper Ashely required more time and work than just applying makeup on a female model.

The only one not wanting to miss this for anything in the world was Keira, and so she instantly complained. “I have nothing else to do than be here and watch so I’ll join you. I wouldn’t want to miss this at all, I bet it’ll be awesome.” She exclaimed enthusiastically. 

Jessy had taken an instant dislike to Keira, unlike the rest of the team she didn’t know her yet, but from where she stood it looked like she wanted nothing more than to mock Ash which was something Jessy couldn’t stand, having seen way to many of her clients scared because of people like this. “You have no business watching anything but the shoot, so unless you go find something else to do in the meantime, I’ll be on my way home again.” Jessy said assertively, applying what pressure she could.

It was enough pressure to get Beatrice involved. “That won’t be necessary Jessy, we’re very happy to have you here and I’m sure Keira will find something else to do in the meantime, now won’t you Keira?” She asked her daughter raising an eyebrow to let her know she was dead serious. From what work she had seen no one in the area was as good at this as Jessy was. If she wanted the best possible chance to pitch Ash instead of that model who had fallen on her face then she needed Jessy. Besides if Jessy left not only would she lose the best for this task, but also the only makeup artist present.

Keira wanted to protest again, she wasn’t happy with how Jessy was ruining this opportunity to further mock her brother at all. With her mother’s stern gaze she could do nothing but give in though and the more she thought about it, the more she realised she had to take a step back. Without Jessy there would be no proper shoot at all. “Alright, I’ll go for a walk.” She finally said reluctantly.

“Great, Ashley, would you mind following along? It’s about time we’d get started.” Jessy said entering one of the bedrooms which had been changed to makeup and dressing room. Quietly Ash followed along deeply grateful for how Jessy had stood up to Keira. He didn’t look forward to being ‘transformed’ in front of all these people, but if it needed to happen anyways then he was glad it would be Jessy who would be doing it.

Jessy led Ash into the room then quickly went over to her car to get her stuff before coming back, locking the door to the room so they certainly wouldn’t be disturbed. “Hey Ashley, don’t worry to much about your sister and her mockery. I think you look gorgeous already and with a little help I’m sure you’ll shine like never before. Now I know that this probably isn’t quite comfortable for you, but I’m going to have to ask you to strip, and that pretty much completely I’m afraid. I was informed that you’ll modelling lingerie as well and there for a gaff is definitely advised, do you know what a gaff is?” Jessy asked patiently and warmly.

It came as a bit of a shock to Ash, but at the same time her tone also put him at ease slightly. “I know what a gaff is.” He replied softly. He had come across it a couple of times during online searches, but he had never actually seen one up close or worn one.

“Great, if you want you can put it on yourself and I’ll give you some privacy to do so, if you need help however you can always call out for me.” Jessy said respectful of Ash’s privacy. She then handed him a small skin coloured thong style thing that looked slightly padded at the crotch before turning around allowing him privacy.

Slightly embarrassed Ash took the garment and first stripped out of his current clothes. He then followed what he had once read online, pushing his balls up in their cavities before tucking his penis back and pulling the tight gaff in place keeping everything flat, giving him a crotch that resembled that of a barbie doll. “I’m done.” Ash spoke softly, grateful for how patient Jessy was being. She managed to put him at least a little at ease in this nerve wrecking situation. 

“Alright, up next I’m going to help you with some silicone hip pads and breast forms, once they’ll warm to the skin they’ll feel pretty realistic and with some makeup to blend them exactly to your skin they’ll look real as well. This can be a little shocking to most people as it really does create a nice hourglass shape, but after a little getting used to the sight most people are thrilled with the look it offers them.” Jessy carefully explained the next steps, taking out the silicone forms closely resembling Ash’s skin tone.

“So Ashley, are you excited for your very first shoot as a girl? How comes your sister is being such a pardon the word bitch though? “ Jessy asked making some small talk while trying to get a better grasp of the situation after seeing the interactions with his sister and the slight fear in Ash’s eyes she had somewhat mixed feeling about this project.

Ash remained silent for a few minutes, not really certain about what he should or shouldn’t say to this woman. Jessy didn’t push though. She just casually kept on working, rubbing the glue for the hip pad on the entire area of skin they would cover as if it was the most normal thing in the world.

Eventually Ash decided to open up anyways, if only to break the silence. Jessy was being very nice and non-judgemental. The whole vibe he got of her was one of support and casual acceptance as if this was just a normal situation. On top of that he also just felt the need to vent what had happened and there was no one else he could really vent to without revealing his secret he so desperately guarded.

“Well I wasn’t supposed to be here, this wasn’t supposed to happen. I just kind of stole one of my sister’s skincare products then somewhere in the confrontation I said something along the lines of that even I would make a prettier girl than she did. Then the argument got heated and she drug me to my moms office. My mom basically agreed that I should put my money where my mouth is and prove that I could make a prettier girl.” Ash started.

“This then led to her claiming I shouldn’t be expected to know how to do makeup and such as well as my sister so that for the most objective view we would need professional help and a professional shoot. I guess this is it.” Ash finished.

Jessy looked up somewhat shocked. “So you mean to say that they forced you into all of this because of a stupid bet made during an argument? I’m sorry, but I won’t participate in that kind of thing.” Jessy exclaimed dead serious.

A wave of panic rushed over Ash, what would his mother say if he ruined this, besides, as nervous as he was, there was also a small voice deep inside of him that wanted his secret dream of becoming a model to become reality. “Wait!” he screamed out making Jessy who was already on her way to give Beatrice and Keira a piece of her mind freeze in her tracks.

“It has also always been somewhat of a fantasy of mine, but no one knows, and please don’t tell anyone.” Ash blurted out, shocked that he literally confessed his secret to someone. His sister might have had a glimpse of his secret when she found that outfit in his closet and saw his makeup skills, but now he had gotten the full extend of it out for the first time in his life. It came as a shock to him, but also as a huge relief.

Instantly Jessy’s determination to stop this ended as she made her way back to Ash with a compassionate look on her face. “Oh sweetie, don’t you worry, I’ll keep your secret. I promise. Now I understand why you’re so nervous, but if it’s any help, you do make a very pretty girl. I understand that giving in to your true self, especially one so different than the body you have gotten and the way you have been raised is hard, but please don’t let that get in the way of enjoying this. Besides your secret will remain safe as you have the perfect excuse for this shoot right?” Jessy said compassionate, trying to put Ash at ease so he could enjoy this secret fantasy.

“Now let’s continue getting you ready shall we?” Jessy asked as she went back to work applying the other hip pad before using her makeup kit to make the pads blend perfectly to Ash’s skin. When she started applying the glue for the breast forms she was surprised to feel and see the light swelling that was consistent with some of her clients on hormones. With how badly Ash wanted to keep this secret this raised an alarm in her head though.

“No one knows about this secret of yours, right? Also not your doctor or anyone like that?” Jessy asked trying her best to not sound worried. She wanted an honest answer, but this was too important to let slip so she needed to be slightly persistent as well.

“Of course no one knows about it.” Ash blurted out.

“Oh I just thought that at least your mother or doctor would know since you are on hormones.” Jessy replied casually curious to see his reaction. She didn’t want to upset Ash at all, but wanted his shocked reaction told her all she needed to know. Just like she feared he was on underground hormones. She had seen it happen a couple of times already and while it wasn’t instantly harmful messing with things like that unregulated could cause big trouble.

Before he could speak up Jessy took the word. “Look Ash, I’m not mad and I don’t want to upset you, but I would like to urge you not to take those underground meds, they can really mess with your body in a bad way if you aren’t careful. You’re old enough to go to a doctor on your own and make the decision yourself, but if you want I could come with you. Your family doesn’t have to know, at least not yet, but it’s important that if you want to stay on hormones that you follow a regulated program. Of that I can assure you.” Jessy said voicing her concern.

Ash didn’t really know what to say, he had never really thought about the dangers, only the results, but he realised this woman might be right. He still didn’t know though, what if his mother would find out? “Just think about it okay, and please don’t take those underground meds anymore.” Jessy said concerned but judgement free.

Shocked Ash just stood there. He had been on these things for a while and he had been concerned when he had started feeling the slight lumps form at his nipples. They were still very small and practically invisible. They were most noticeable to the touch which had allowed him to get away with keeping his secret all this time. It was something he wanted to keep this way, but feared he would be unable to if those lumps kept growing. Still he had always pushed it away as worries for later.

Apart from those small but growing lumps he had never really worried about any other dangers, but Jessy was probably right. He’d better stop using these black-market hormones all together. Going to a doctor was probably wise as well, but that would get him an official record and he was terrified that his mom or god forbade his sister would ever find out his secret. It was crazy in a way, that Jessy this girl he had only just gotten to know already knew him on a way deeper, more intimate level than anyone else. He had never confided his secret to anyone before.

“I just took them to keep myself from bulking up while working out, so I could just blame my lack of beefy muscle growth on genetics. You’re right though, I should probably stop, but if I suddenly stop working out it won’t go unnoticed and I don’t want to bulk up.” Ash finally said to Jessy who was sticking the breast forms to his chest now.

She gave him a compassionate smile back. “I’m very glad you agree that those things are bad for you and if you want I know a doctor who’s specialised in these kind of things who knows how difficult it is to be yourself in the face of judgement. She can definitely arrange to make this strictly confidential to the point where even your family doctor won’t know. Of course if you get other meds you would also have to contact her to see if it won’t have a negative effect in combination with your hormone treatment.” Jessy said seeing how Ash remained worried none the less.

“If you’re still worried about those potentially bad side effects, you can stop now. I mean you look very healthy to me meaning that there probably isn’t a problem yet, but one wrong batch could mean a disaster so it’s important to stop it either way. If you decide to continue with this hormone treatment in a regulated fashion however you will have to come clean to your mother and everyone eventually. Those lumps will only grow in time and you won’t be able to hide it forever. It’s not an immediate issue just yet, but you need to be realistic as well.” Jessy said.

“Yeah, I know, it’s just what will they think or say if I tell them?” Ash replied mainly thinking about his sisters Laughter and the way she’d probably try to humiliate him over it. 

“Well I can’t talk for your sister as she does seem to have it out for you, but the fact that your mom hired me and set all this up at least means she is somewhat open to the idea already. Of course I don’t know how she’ll react, but I don’t think she would have set all of this up if she just wanted to let your sister make fun of you now would she?” Jessy argued.

Ash had never really thought about it that way, but she was probably right. This was a whole lot of effort just to make fun of him meaning that this probably wasn’t to make fun of him in the first place. It made him feel a little better about this whole situation already.

“Besides just take a look at yourself, you’re gorgeous already. You don’t even really need the makeup to look amazing. You look rather passable already now that you’ve just gotten a more feminine shape.” Jessy commented as she finished blending the hip and breast forms to match Ash’s skin perfectly. Turning him towards the big full-length mirror she giggled lightly when she saw the shocked awe spread across his face.

The shock mainly came from not being able to believe what he was seeing. Jessy was right, he did look gorgeous, his waist might not have been pulled in but the pads definitely provided an hourglass figure. If anything Ash looked pretty much like a barbie doll of sorts, mainly because his crotch was entirely flat. The shock quickly turned to admiration as Jessy just stood there smiling at the side. This was the exact look she always went for, the look that made her job so very worth it. Seeing her customers who often had issues with their bodies admire themselves like this was the best thing ever.

Still amazed by his appearance Ash poked his breast forms. They looked so very real even though he knew and could feel that they weren’t real. It was amazing yet somewhat freaky as well, how would his mother and sister react upon seeing him like this?

“I can imagine you’d want to cover those up before I call Sarah in for your hair right? I was told that these would be part of your first outfit.” Jessy said holding out a soft pink lacey push up bra and matching thong. It was a very sexy lingerie set one Ash took an instant liking to. Weirdly enough, he actually felt somewhat okay imagining having to model it. Seeing the work Jessy had already done had boosted his confidence by a lot. He knew he would be able to count on her to do a magnificent job on the makeup as well. Jessy had been right the best he could do was just enjoy the ride and the shoot. It was after all one of his dreams and Keira forcing him gave him the perfect excuse to still maintain his secret.

In no time Ash was dressed in the sexy ensemble, smiling broadly at his reflected image. Hooking the bra behind his back didn’t give him the slightest bit of problems. With the lingerie he looked even more like a real girl than he had before. Especially thanks to the panties. They covered up the weirdly flat groin created by the gaff in panties it looked nice, without the sexless part just looked rather alien. 

“You can also put this on for a bit of extra coverup while getting ready if you want. It’s the way most models are dressed in the make up room so…” Jessy started but was cut short when Ash suddenly pulled her in for a tight hug, giving her a kiss on her cheek.

“Thank you so much Jessy, you have done an amazing job, I was insanely nervous for today, to the point of dreading the whole experience but you have helped me a ton. You’re the best.” He said as he let go an took the white silk bathrobe Jessy had offered him to wear. Throwing it on Ash arranged the garment in such a way that it showed a slight bit of cleavage, the very cleavage Jessy had just created. It still felt somewhat wrong, but it also felt so right at the same time.

His little action didn’t go unnoticed by Jessy who was smiling broadly. Ash had certainly blossomed a lot in the short time they spent together and seeing it really warmed her heart. For a moment she had thought about quitting this job when Ash had informed her that he was forced into this, but right now she was so very happy that he had come clean to her about his own desires and secret after all. Maybe this shoot could prove to be a first step to self-acceptance for him making it worth way more than the money she would make of this for Jessy.

“Alright, can I call Sarah in for your hair while I start on your makeup? Jessy eventually asked after giving Ash some more time to admire himself now that he was somewhat dressed. The silk bathrobe didn’t do much as far as cover up went, but it preserved some modesty at least. That and it actually made him feel slightly sexy.

“Yes, I’m curious to see what I’ll look like once everything is done, I’m sure it’ll be spectacular. Just one request, can you please remain quiet when she’s in here? I mean definitely as far as my secret and these hormones go. If she knows then surely Keira will know shortly after and if she does then I won’t hear the end of it.” Ash requested somewhat nervously yet slightly excited as well.

“Of course, no one will hear a word from me. It isn’t to me to decide when and to who you talk about this. Just know that you’re always free to chat about it with me if you wish. I’ll give you my number sometime later on and if you’re ever in need of a talk and you don’t have anyone to talk about what you want we can always meet up. The same goes if you want to take me up on that offer to accompany you to the doctor.” Jessy said with a kind and reassuring smile.

Put at ease Ash took place in the makeup chair, trying not to show the inner excitement he felt towards getting all prettied up by professionals, afraid Sarah would otherwise pick up on it. Jessy left the room for a quick moment and about a minute later she entered the room with Sarah who had a big grin on her face, a look that quickly changed into a dropping jaw as she noticed the amazing transformation Ash had been through so far.

Quickly recovering she spoke up. “Oh my god Ashley, is that really you? I can hardly believe it, if I didn’t know better I would have thought you were a real woman, I mean that cleavage just looks so realistic that and you don’t have the most manly face either especially not with those thin brows.” She gushed. It was clear that at the start she had entered with the idea of poking some slight fun at him, but seeing the results so far it was hard for her to be anything but amazed;

“Thank you, it took a lot of practice to learn how to play around with blending and shadows this much. Now do you need any help with the hair? Otherwise I’ll get to work on the nails.” Jessy spoke up, diverting the attention away from Ash who looked a bit uncomfortable with Sarah’s excitement.

It worked perfectly as Sarah instantly turned her attention to Ashe’s hair. “Oh no, no help needed at all. Her hair is really well kept and shouldn’t be giving me much trouble. I think the best approach for this shoot would just be adding some extensions and giving it a good brushing and slight curling to add some volume and a slight wave for a seemingly effortless glamourous hairdo.” She said assessing the situation in a way that it would be perfect to pitch in a portfolio destined for a hair product ad.

“Great then I’ll get to work on her nails, I’ll save the makeup for once you’re done with the hair.” Jessy commented mainly staying quiet like Ash had requested. Sarah also became rather quiet once she started on his hair, selecting the right coloured extensions and starting the laborious task of weaving them in with his real hair before cutting it up till his hair now reached his mid back. Ash was rather surprised at just how much extra weight these extensions added.

While Sarah was busy with the hair Jessy gave Ash a French tipped manicure and pedicure. For his hands she applied a set of one-inch gel nails, shaping them in neat ovals instantly making his hands look daintier and more feminine. While Ash was a bit nervous about these changes, he did secretly like the full beauty treatment he was getting. He didn’t show it though afraid of what Sarah might think.

The whole treatment took nearly an hour and when Sarah finished up his hair Jessy addressed her once more. “Could you please leave now while I do the makeup? I want it to be a surprise when it’s done and it’s time for the reveal.” She claimed to the hairdresser, searching for an excuse to get her out of the room so Ash could talk more freely once more.

“Oh okay, sure thing, you’re the artist. I’m really curious to see how it’ll turn out. I bet it’ll look amazing, I mean it already does so I’m sure of it, but I’m still curious.” Sarah said somewhat excited, not bothering to argue. While she did want to stay to watch she was also looking forward to be blown away by the full metamorphose.

Once she was gone Jessy excitedly covered up all mirrors. Ash might not have been turned to one and so he hadn’t seen his new hair just yet, but she had to admit Sarah really knew what she was doing when it came to hair. Ash’s new locks simply looked amazing. She didn’t want to keep secrets from him, but at the same time she wanted to see his reaction once the full effect was revealed. She was certain he would love it.

“Now forgive me for covering up the mirrors, but I really want to see how you’ll react to the full-on transformation effect. Are you willing to allow me that small pleasure?” Jessy asked excitedly as she picked up her brushes and makeup to start working.

“Uhm yeah sure, I trust you. By the way having my hair and nails done like this did feel really nice I have to admit that. Can you maybe explain how you applied everything afterwards so maybe I can take a shot at it if I really like the look?” Ash asked, visibly relaxing now that he was alone with Jessy once more. It was strange but pleasant to be able to trust someone so completely even though they had only just met.

“Most certainly, I’d love to show you for sure. To be honest your face is way easier to work on than most of my client’s faces. You have rather delicate features already so I’m certain the end result will simply be amazing.” Jessy exclaimed excitedly, very pleased to hear that Ash trusted her.

For the next half an hour she attacked Ash’s face with a variety of brushes and tubes before finally stepping back to have a last check up of her work and to see if anything needed to change. Inspecting his face carefully she was very proud of her work. Ash came out looking way better than even she had imagined. One of the trickiest parts had actually been to give his thinly plucked brows a more voluminous yet natural look.

The entire look revolved around keeping things natural while enhancing his eyes and lips a little to really make them stand out. Since Ash would be posing for a variety of vastly different things, ranging from casual to classy and even boudoir shots, Jessy had determined that natural would be the best look. His eyelids were had received a very light smoky coating along with some eyeliner and mascara too make his bright blue eyes really stand out without being too noticeable or tacky. His lips had gotten a slight redder coating with a wet look to them enhancing them in a subtle way.

“Alright Ashely, are you ready for the grand reveal? I’m honestly jealous of just how great you’re looking right now. You can rival the prettiest girls if I do say so myself.” Jessy said excitedly, building Ash’s curiosity. Ever since Jessy had covered up those mirrors his curiosity had grown even though he hadn’t really looked in the mirror after Sarah was done with his hair.

“I’m ready, please just uncover those mirrors, I’m dying to see how I ended up looking.” Ash said sharing in Jessy’s excitement. Her excitement told him that he probably ended up looking rather good, but nothing could have prepared him for the absolutely spectacular end result when Jessy finally uncovered that mirror.

Staring back at him was a girl that looked like she had just stepped off the cover of a magazine, a gorgeous blonde with long wavy hair and a pretty face, just a hint of pink lace teasingly sticking out of her bathrobe’s cleavage. In complete disbelieve Ash brought a hand up to his shocked mouth only to see the woman in the mirror raising a perfectly manicured hand to her gaping mouth. The work Jessy had done nearly felt like magic seeing this spectacular end result. He really did look like a woman, a gorgeous one at that. He knew full well that it was mainly makeup, shading to make his facial features even more delicate, a gorgeous hairdo and of course the prosthetic pads. This was by no mean something he could do on the daily, at least not in this spectacular fashion as everything combined had nearly taken four hours to put together.

It was however a glimpse at how gorgeous of a woman he could make if he followed a real stronger but regulated hormone treatment instead of the black-market testosterone blockers he took now. Overcome with joy he pulled Jessy into another tight hug. “Oh god this is unbelievable, thank you so very much for all of this, this is spectacular, exceeding all my expectations.” Ash exclaimed before blushing and lowering his voice a little, afraid that people outside might pick up on the conversation and figure out his secret.

“You are very welcome honey and If I’m honest you’ve exceeded my expectations as well. You look gorgeous. Now are you ready to show yourself to the others and start your shoot? I know you must be nervous, but just try to have fun. Your mother hired me, your sister set you up, and I just did my job. No one has to know how happy you are with this makeover until you’re ready to tell them.” Jessy told him, it was probably still too soon for him to truly see that he didn’t need to be embarrassed over who he was, but if he could start out enjoying his shoot without worries it would be a huge step in the right direction and Jessy fully planned on making it as enjoyable as possible for him.

Despite her words of encouragement however she could see the nerves and worries return to his face, knowing it was time to show himself to the others. He knew Jessy was right and that it was silly to be embarrassed about this situation he was forced into yet he just couldn’t help it. His new look did give him some increased confidence however and after taking a few deep breaths he finally opened the door and stepped out in the hall, heading to the living/shooting room nervous, but also proud in a way.

As the door opened everyone immediately turned their attention to him and just like his jaw had dropped before seeing the results so did everyone else’s. Even Keira, who had looked bored at first having had to wait for so long without being able to poke fun at her brother like she imagined she could today, looked genuinely amazed. Keira’s amazement quickly soured into a somewhat angry look however. She was jealous beyond believe, jealous that Ash really made a way prettier girl than she ever could and angry that her plans to maker her brother look and act as the biggest sissy freak possible had been soiled. Instead he ended looking like what even she had to admit was a gorgeous woman and she knew everyone else here thought so as well.

Beatrice had to do more than a double take seeing her son all made up like he was. If she didn’t know any better she would have thought that Ash had sneaked out of a window out back and a female model had taken his place. His resemblance to herself when she was young and still a model was freaky for sure, hell Ash possibly looked even more gorgeous than she had been so many years ago. 

Ash looked every bit like the gorgeous daughter she had always wanted to follow in her footsteps. In away it was a pity, a pity that he was actually her son and that this was all just for a day. One thing was for sure though, if this didn’t convince the hair product company that she had found the perfect suitable replacement for their original model of choice then she didn’t know what would. Hell Ash looked better than that girl ever did even if she did say so herself.

**Author's Note:**

> Hello,
> 
> If you liked this work considre checking out my twitter at: https://twitter.com/FibaroSmut
> 
> Kindest regards,  
> Fibaro


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